HCID 86757422, compound → HCID 18536864, compound

HRID 1597108Notes

Reaction equation

[ClH:1].CC(C1C=CC=CC=1[N:11]=[C:12]([C:14]1[S:15][C:16]([S:25][CH3:26])=[C:17](N)[C:18]=1C1N=CSC=1)[NH2:13])C.Br.[CH3:28][CH:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[NH:37][C:38]1[S:39][CH:40]=[C:41](C2C=C(C(OC)=S)SC=2C)[N:42]=1)[CH3:30]>>[ClH:1].[CH3:30][CH:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][C:32]=1[NH:37][C:38]1[S:39][CH:40]=[C:41]([C:17]2[CH:18]=[C:14]([C:12]([NH2:13])=[NH:11])[S:15][C:16]=2[S:25][CH3:26])[N:42]=1)[CH3:28]

Participants

Reactant 2

HCID 86757422HCID 86757422, compound

HCID 86757424HCID 86757424, compound

Product 1

HCID 18536864HCID 18536864, compoundYield 88%

Procedure

4-(2-{[2-(Methylethyl)phenyl]amino{(1,3-thiazol-4-yl))-5-methylthiothiophene-2-carboxamidine hydrochloride: Methyl 4-(2-{[2-(methylethyl)phenyl]amino}(1,3-thiazol-4-yl))-5-methylthiothiophene-2-carboxylate hydrobromide (33.1 mg, 0.06 mmol) was treated as described in Example 154, step (b) to give 22.4 mg (88%) of 4-(2-{[2-(methylethyl)phenyl]amino}(1,3-thiazol-4-yl))-5-methylthiothiophene-2-carboxamidine hydrochloride. 1H NMR (DMSO-d6, 300 MHz) δ 1.19 (d, 6H, J=6.8 Hz), 2.70 (s, 3H), 3.32 (m, 1H), 7.04 (s, 1H), 7.14-7.25 (m, 2H), 7.35 (dd, 1H, J=1.4, 7.5 Hz), 7.86 (dd, 1H, J=1.4, 7.9 Hz), 8.37 (s, 1H); Mass Spectrum (ESI) m/z calcd. for C18H20N4S3, 388.58 (M+H), found 389.2.

Sources & evidence

ORD record: ord-49d9e83e2586405b8ccce13b65ce9a8c
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06291514B1

Reaction notes

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